Substituted carbamoylpyrazolines

ABSTRACT

The invention relates to new substituted carbamoylpyrazolines    &lt;IMAGE&gt;  (I)  to processes in their preparation, and to their use as pesticides.

The invention relates to new substituted carbamoylpyrazolines, toprocesses for their preparation, and to their use as pesticides.

It has been disclosed that certain pyrazoline derivatives have a goodactivity against animal pests.

See, in this context, for example DE-A 2,700,258, U.S. Pat. No.4,174,393, DE-A 2,529,689, U.S. Pat. No. 4,070,365 and EP-A 0,466,408.

However, the level, or duration, of action of these previously knowncompounds is not satisfactory in all fields of application, inparticular in connection with certain organisms or when lowconcentrations are applied.

New substituted carbamoylpyrazolines of the general formula (I) ##STR2##in which R¹ represents an azolinone, azolinethione or azolineiminoradical, each of which is optionally substituted and bonded vianitrogen,

R² represents hydrogen, alkyl, optionally substituted cycloalkyl,halogenoalkyl, halogenoalkylthio or alkoxycarbonyl,

R³ represents hydrogen, alkyl or a group ##STR3## in which R⁷ and R⁸ ineach case independently of one another represent hydrogen, alkyl or aryland

R⁹ represents hydrogen, alkyl or aryl and

n represents the numbers 1 to 6,

R⁴ represents hydrogen or alkyl,

R⁵ represents hydrogen, alkyl, phenyl or alkylthio,

R⁶ represents optionally substituted alkyl, optionally substitutedcycloalkyl or the radical ##STR4## in which R¹⁰ and R¹¹ can be identicalor different and represent hydrogen, halogen, alkyl, nitro, cyano,halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio,optionally substituted phenoxy, optionally substituted mono- ordialkylamino, optionally substituted cycloalkyl, alkoxycarbonyl,optionally substituted arylthio, alkenyloxy, alkinyl, alkylthionyl,alkylsulphonyl, halogenoalkylthionyl, halogenoalkylsulphonyl,halogenoalkoxycarbonyl, or in which R¹⁰ and R¹¹ together represent abivalent radical which optionally contains one or two oxygen atoms andwhich is optionally substituted,

X represents oxygen or sulphur and

Y and Z can be identical or different and represent hydrogen, alkyl,halogen, halogenoalkyl, alkoxy, alkylthio, halogenoalkoxy,halogenoalkylthio, alkoxycarbonyl, halogenoalkoxycarbonyl, optionallysubstituted aryloxy, optionally substituted arylthio, alkenyloxy,alkinyl, alkylthionyl, alkylsulphonyl, halogenoalkylthionyl,halogenoalkylsulphonyl, nitro, or cyano, or in which Y and Z togetherrepresent 3,4-methylenedioxy or 3,4-ethylenedioxy, each of which isoptionally substituted by halogen,

have now been found.

Furthermore, it has been found that the new substitutedcarbamoylpyrazolines of the general formula (I) ##STR5## in which R¹represents an azolinone, azolinethione or azolineimino radical, each ofwhich is optionally substituted,

R² represents hydrogen, alkyl, optionally substituted cycloalkyl,halogenoalkyl, halogenoalkylthio or alkoxycarbonyl,

R³ represents hydrogen, alkyl or a group ##STR6## in which R⁷ and R⁸ ineach case independently of one another represent hydrogen, alkyl or aryland

R⁹ represents hydrogen, alkyl or aryl and

n represents the numbers 1 to 6,

R⁴ represents hydrogen or alkyl,

R⁵ represents hydrogen, alkyl, phenyl or alkylthio,

R⁶ represents optionally substituted alkyl, optionally substitutedcycloalkyl or the radical ##STR7## in which R¹⁰ and R¹¹ can be identicalor different and represent hydrogen, halogen, alkyl, nitro, cyano,halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio,optionally substituted phenoxy, optionally substituted mono- ordialkylamino, optionally substituted cycloalkyl, alkoxycarbonyl,optionally substituted arylthio, alkenyloxy, alkinyl, alkylthionyl,alkylsulphonyl, halogenoalkylthionyl, halogenoalkylsulphonyl,halogenoalkoxycarbonyl, or in which R¹⁰ and R¹¹ together represent abivalent radical which optionally contains one or two oxygen atoms andwhich is optionally substituted,

X represents oxygen or sulphur and

Y and Z can be identical or different and represent hydrogen, alkyl,halogen, halogenoalkyl, alkoxy, alkylthio, halogenoalkoxy,halogenoalkylthio, alkoxycarbonyl, halogenoalkoxycarbonyl, optionallysubstituted aryloxy, optionally substituted arylthio, alkenyloxy,alkinyl, alkylthionyl, alkylsulphonyl, halogenoalkylthionyl,halogenoalkylsulphonyl, nitro, or cyano, or in which Y and Z togetherrepresent 3,4-methylenedioxy or 3,4-ethylenedioxy, each of which isoptionally substituted by halogen,

are obtained when

A) to obtain carbamoylpyrazolines of the formula (I) in which R⁵represents hydrogen, pyrazoline derivatives of the formula (II) ##STR8##in which Y, Z, R¹, R², R², R³ and R⁴ have the abovementioned meaning

are reacted with isocyanates or isothiocyanates of the formula (III)

    X=C=N=R.sup.6                                              (III)

in which X and R.sup. 6 have the abovementioned meaning,

if appropriate in the presence of bases,

or when

B) to obtain carbamoylpyrazolines of the formula (I) in which R.sup. 2represents alkyl, cycloalkyl, halogenoalkyl, halogenoalkylthio oralkoxycarbonyl, compounds of the formula (IV) ##STR9## in which X, Y, Z,R¹, R³, R⁴, R⁵ and R⁶ have the abovementioned meaning, are reacted withcompounds of the formula (V)

    Hal-R.sup.2-1                                              (V)

in which

Hal represents halogen and

R²⁻¹ represents alkyl, optionally substituted cycloalkyl, halogenoalkyl,halogenoalkylthio or alkoxycarbonyl,

in an anhydrous medium and with addition of a strong base.

Finally, it has been found that the new carbamoylpyrazolines of thegeneral formula (I) have a very good activity against pests and, inparticular, are very good insecticidal and acaricidal activity.

Surprisingly, the substituted carbamoylpyrazolines according to theinvention display a considerably better insecticidal activity againstinsects and arachnids which are phytopathogenic and which parasitisewarm-blooded species than compounds which are similar chemically andfrom the point of view of their action and which are known from theprior art.

Formula (I) provides a general definition of the substitutedcarbamoylpyrazolines according to the invention. Preferred compounds ofthe formula (I) are those in which

R¹ represents an azolinone, azolinethione or azolineimino radical,optionally monosubstituted or disubstituted by identical or differentsubstituents and bonded via nitrogen, from the series comprising##STR10## in which

one of the groups A or B represents nitrogen and in each case the otherone (B or A) represents oxygen, sulphur or the group --N alkyl(C₁ -C₄)or a methylene group --CH₂ --,

W represents oxygen, sulphur or the group --N alkyl(C₁ -C₆),

the following substituents being suitable: alkyl (C₁ -C₆), alkoxy(C₁-C₆), alkyl(C₁ -C₆)thio, amino, alkyl (C₁ -C₆)amino, halogenoalkyl (C₁-C₄), dialkyl (C₁ -C₆) amino, and phenyl which is optionally substitutedby halogen, alkyl(C₁ -C₄), alkoxy(C₁ -C₄), halogenoalkyl(C₁ -C₄),halogenoalkoxy(C₁ -C₄)- or halogenoalkyl (C₁ -C₄)thio,

R² represents hydrogen, alkyl (C₁ -C₆), or represents cycloalkyl(C₃ -C₇)which is optionally substituted by halogen or halogenoalkyl-(C₁ -C₄); orrepresents halogenoalkyl (C₁ -C₄), halogenoalkyl (C₁ -C₄) thio oralkoxy(C₁ -C₆)carbonyl,

R³ represents hydrogen, alkyl(C₁ -C₆) or a group ##STR11## in which R⁷and R⁸ in each case independently of one another represent hydrogen,alkyl (C₁ -C₆), or phenyl which is optionally substituted by alkyl (C₁-C₄), alkoxy(C₁ -C₄), alkyl(C₁ -C₄)thio, halogen, halogenoalkyl(C₁ -C₄),halogenoalkoxy(C₁ -C₄) or halogenoalkyl(C₁ -C₄) thio and

R⁹ represents hydrogen, alkyl(C₁ -C₆) or optionally substituted phenyl,suitable substituents being the phenyl substituents mentioned in thecase of R⁸, and

n represents the numbers 1 to 4,

R⁴ represents hydrogen or alkyl (C₁ -C₆),

R⁵ represents hydrogen, alkyl(C₁ -C₆), phenyl or alkyl(C₁ -C₆)thio,

R⁶ represents alkyl (C₁ -C₆) which is optionally substituted by halogen,halogenoalkyl(C₁ -C₄) or halogenoalkoxy(C₁ -C₄), or representscycloalkyl(C₃ -C₇) which is optionally substituted by halogen,halogenoalkyl(C_(-C) ₄) or halogenoalkoxy(C₁ -C₄), or represents theradical ##STR12## in which R¹⁰ and R¹¹ can be identical or different andrepresent halogen, alkyl(C₁ -C₆), nitro, cyano, halogenoalkyl(C₁ -C₄),alkoxy(C₁ -C₆), halogenoalkoxy(C₁ -C₄), alkyl(C₁ -C₄)thio,halogenoalkyl(C₁ -C₄)thio, or represent phenoxy or phenylthio, each ofwhich is optionally substituted by halogen, halogenoalkyl (C₁ -C₄) oralkoxy(C₁ -C₄), or represents mono- or dialkylamino, each of which has 1to 6 carbon atoms in the alkyl radical and each of which is optionallysubstituted by halogen, alkoxy(C₁ -C₄) or halogenoalkyl(C₁ -C₄ ), orrepresent cycloalkyl (C₁ -C₇) which is optionally substituted by alkyl(C₁ -C₄), alkoxy(C₁ -C₄), halogen or alkyl (C₁ -C₄)thio, or representalkoxy(C₁ -C₄) carbonyl, alkenyl(C₂ -C₆)oxy, alkinyl(C₂ -C₆), alkyl (C₁-C₄)thionyl, alkyl (C₁ -C₄)sulphonyl, halogenoalkyl (C₁ -C₄)thionyl,halogenoalkyl (C₁ -C₄)sulphonyl or halogenoalkoxy(C₁ -C₄)carbonyl, or inwhich

R¹⁰ and R¹¹ together represent one of the following bivalent radicals##STR13## X represents oxygen or sulphur and Y and Z can be identical ordifferent and represent hydrogen, alkyl(C₁ -C₆), halogen,halogenoalkyl(C₁ -C₆), alkoxy(C₁ -C₆), alkyl(C₁ -C₆)thio,halogenoalkoxy(C₁ -C₄), halogenoalkyl(C₁ -C₄)thio, alkoxy (C₁ -C₄)carbonyl, halogenoalkoxy(C₁ -C₄ ) carbonyl, or represent phenoxy orphenylthio, each of which is optionally substituted by halogen, alkyl(C₁-C₄), alkoxy(C₁ -C₄) or halogenoalkyl(C₂ -C₄), or represent alkenyl (C₂-C₆)oxy, alkinyl (C₂ -C₆ ), alkyl(C₁ -C₄)thionyl, alkyl (C₁-C₄)sulphonyl, halogenoalkyl (C₁ -C₄)thionyl, halogenoalkyl (C₁ -C₄)sulphonyl, nitro or cyano, or in which

Y and Z together represent 3,4-methylenedioxy or 3,4-ethylenedioxy, eachof which is optionally substituted by fluorine and/or chlorine.

Particularly preferred compounds of the formula (I) are those in which

R¹ represents an azolinone, azolinethione or azolineimino radical,optionally monosubstituted or disubstituted by identical or differentsubstituents and bonded via nitrogen, from the series comprising##STR14## in which

one of the groups A or B represents nitrogen and in each case the otherone (B or A) represents oxygen, sulphur or the group --N alkyl(C₁ -C₄)or a methylene group --CH₂ --,

W represents oxygen, sulphur or the group --N alkyl(C₁ -C₄)

and the following substituents being suitable: alkyl(C₁ -C₄), alkoxy(C₁-C₄), alkyl(C₁ -C₄)thio, amino, alkyl(C₁ -C₄)amino, halogenoalkyl(C₁-C₄), dialkyl(C₁ -C₄) amino and phenyl which is optionally substitutedby fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy,halogenoalkyl(C₁ -C₂), halogenoalkoxy(C₁ -C₂) or halogenoalkyl (C₁-C₂)thio,

R² represents hydrogen, alkyl (C₁ -C₄), or cycloalkyl (C₃ -C₆) which isoptionally substituted by fluorine, chlorine, bromine orhalogenoalkyl(C₁ -C₃); or represents halogenoalkyl (C₁ -C₃ ),halogenoalkyl(C₁ -C₃)thio or alkoxy(C₁ -C₄)carbonyl,

R³ represents hydrogen, alkyl (C₁ -C₄) or a group ##STR15## in which R⁷and R⁸ in each case independently of one another represent hydrogen,alkyl(C₁ -C₄), or phenyl which is optionally substituted by methyl,ethyl, methoxy, ethoxy, methylthio, ethylthio, fluorine, chlorine,bromine, halogenoalkyl(C₁ -C₂), halogenoalkoxy(C₁ -C₂) orhalogenoalkyl(C₁ -C₂)thio and

R⁹ represents hydrogen, alkyl(C₁ -C₄), or phenyl, which is optionallymonosubstituted or polysubstituted by identical or differentsubstituents, suitable substituents being the phenyl substituentsmentioned in the case of R⁸, and

n represents the numbers 1, 2 or 3,

R⁴ represents hydrogen or alkyl (C₁ -C₄),

R⁵ represents hydrogen, alkyl(C₁ -C₄), phenyl or alkyl(C₁ -C₃)thio,

R⁶ represents alkyl (C₁ -C₄) which is optionally substituted byfluorine, chlorine, bromine, halogenoalkyl(C₁ -C₃ ) or halogenoalkoxy(C₁ -C₃), or represents cycloalkyl(C₁ -C₆) which is optionallysubstituted by fluorine, chlorine, bromine, halogenoalkyl(C₁ -C₃) orhalogenoalkoxy(C₁ -C₃), or represents the radical ##STR16## in which R¹⁰and R¹¹ can be identical or different and represent fluorine, chlorine,bromine, iodine, alkyl (C₁ -C₄), nitro, cyano, halogenoalkyl (C₁ -C₃),alkoxy (C₁ -C₄), halogenoalkoxy (C₁ -C₃), alkyl(C₁ -C₃)thio orhalogenoalkyl(C₁ -C₃)thio, or represent phenoxy which is optionallysubstituted by fluorine, chlorine, bromine, halogenoalkyl(C₁ -C₃) oralkoxy (C₁ -C₄), or represent mono- or dialkylamino, each of which has 1to 4 carbon atoms in the alkyl radical and each of which is optionallysubstituted by fluorine, chlorine, bromine, alkoxy (C₁ -C₃) orhalogenoalkyl (C₁ -C₃), or represent cycloalkyl(C₃ -C₆) which isoptionally substituted by alkyl(C₁ -C₃), alkoxy(C₁ -C₃), fluorine,chlorine, bromine or alkyl(C₁ -C₃)thio, or in which

R¹⁰ and R¹¹ together represent one of the following bivalent radicals##STR17##

X represents oxygen or sulphur and

Y and Z can be identical or different and represent hydrogen, alkyl (C₁-C₄ ), fluorine, chlorine, bromine, halogenoalkyl (C₁ -C₄), alkoxy(C₁-C₄ ), alkyl (C₁ -C₄)thio, halogenoalkoxy(C₁ -C₃), halogenoalkyl(C₁-C₃)thio, alkoxy(C₁ -C₃ ) carbonyl, or phenoxy or phenylthio, each ofwhich is optionally substituted by fluorine, chlorine, bromine, alkyl(C₁-C₃), alkoxy(C₁ -C₃) or halogenoalkyl (C₁ -C₃), or represent alkenyl (C₂-C₄)oxy, alkinyl(C₂ -C₄), alkyl(C₁ -C₃)thionyl, alkyl(C₁ -C₄)sulphonylhalogenoalkyl (C₁ -C₃)thionyl, halogenoalkyl (C₁ -C₃)sulphonyl, nitro orcyano, or in which

Y and Z together represent 3,4-methylenedioxy or 3,4-ethylenedioxy, eachof which is optionally substituted by fluorine and/or chlorine.

Especially preferred compounds of the formula (I) are those in which

R¹ represents an azolinone, azolinethione or azolineimino radical, ineach case optionally monosubstituted or disubstituted by identical ordifferent substituents and bonded via nitrogen, from the seriescomprising ##STR18## in which

one of the groups A or B represents nitrogen and the other one (B or A)represents oxygen, sulphur or the group --NCH₃ or a methylene group--CH₂ --,

W represents oxygen or sulphur,

and the following substituents being suitable: methyl, ethyl, n-propyl,i-propyl, t-butyl, methoxy, methylthio, trifluoromethyl,chlorodifluoromethyl, fluorodichloromethyl, and phenyl which isoptionally substituted by fluorine, chlorine, bromine, methyl, methoxy,trifluoromethyl or trifluoromethoxy

R² represents hydrogen, methyl, ethyl, n-propyl, i-propyl or alkoxy(C₁-C₂)carbonyl,

R³ represents hydrogen, methyl, ethyl, n-propyl, i-propyl or the group##STR19## in which R⁷ and R⁸ in each case independently of one anotherrepresent hydrogen, methyl, ethyl, n-propyl or i-propyl,

R⁴ represents hydrogen, methyl, ethyl or n-propyl,

R⁵ represents hydrogen, methyl, ethyl, n-propyl, i-propyl, phenyl oralkyl(C₁ -C₂)thio,

R⁶ represents methyl, ethyl, n-propyl or i-propyl, each of which isoptionally substituted by fluorine, chlorine, halogenoalkyl(C₁ -C₃) orhalogenoalkoxy(C₁ -C₃), or represents cycloalkyl(C₃ -C₆) which isoptionally substituted by fluorine, chlorine, halogenoalkyl(C₁ -C₃) orhalogenoalkoxy(C₁ -C₃), or represents the radical ##STR20## in which R¹⁰and R¹¹ can be identical or different and represent fluorine, chlorine,bromine, iodine, methyl, ethyl, n-propyl, i-propyl, tert.-butyl, nitro,cyano, halogenoalkyl(C₁ -C₃), alkoxy(C₁ -C₃), halogenoalkoxy(C₁ -C₃),alkyl (C₁ -C₃)thio, halogenoalkyl(C₁ -C₃)thio, or represent phenoxywhich is optionally substituted by fluorine, chlorine, halogenoalkyl(C₁-C₃), methoxy, ethoxy, methyl or ethyl, or represent mono- ordialkylamino, each of which has 1 to 3 carbon atoms in the alkyl radicaland each of which is optionally substituted by fluorine, chlorine,methoxy, ethoxy or halogenoalkyl (C₁ -C₃ ), or represent cycloalkyl(C₃-C₆) which is optionally substituted by methyl, ethyl, methoxy, ethoxy,fluorine, chlorine or alkyl (C₁ -C₃) thio, or in which

R¹⁰ and R¹¹ together represent one of the following bivalent radicals##STR21##

X represents oxygen or sulphur and

Y and Z can be identical or different and represent hydrogen, methyl,ethyl, n-propyl, i-propyl, fluorine, chlorine, halogenoalkyl (C₁ -C₃),methoxy, ethoxy, n-propyloxy, i-propyloxy, alkyl (C₁ -C₃)thio,halogenoalkoxy (C₁ -C₃), halogenoalkyl (C₁ -C₃)thio, alkoxy (C₁-C₃)carbonyl, or represent phenoxy or phenylthio, each of which isoptionally substituted by fluorine, chlorine, methyl, ethyl, methoxy,ethoxy or halogenoalkyl (C₁ -C₃), or represent alkenyl (C₃ -C₄)oxy,alkinyl(C₂ -C₄), alkyl(C₁ -C₃)thionyl, alkyl (C₁ -C₃)sulphonyl,halogenoalkyl (C₁ -C₃)thionyl, halogenoalkyl (C₁ -C₃)sulphonyl, nitro orcyano, or in which

Y and Z together represent 3,4-methylenedioxy or 3,4-ethylenedioxy, eachof which is optionally substituted by fluorine and/or chlorine.

The meaning of the substituent halogenoalkyl in the radicalshalogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylthionyland halogenoalkylsulphonyl contains preferably 1 to 4, in particular 1or 2, carbon atoms and preferably 1 to 5, in particular 1 to 3,identical or different halogen atoms, suitable halogen atoms preferablybeing fluorine, chlorine and bromine, in particular fluorine andchlorine. Examples which may be mentioned are trifluoromethyl,chlorodifluoromethyl, bromomethyl, 2,2,2-trifluoroethyl andpentafluoroethyl.

The following substituted carbamoylpyrazolines which have the followingformulae and which are listed in Tables 1A to 1I and 1K to 1M may bementioned individually in addition to the compounds mentioned in thepreparation examples:

                                      TABLE 1A                                    __________________________________________________________________________     ##STR22##                                                                    Y      Z X R.sup.2                                                                              R.sup.3                                                                         R.sup.4                                                                         R.sup.5                                                                         R.sup.6                                               __________________________________________________________________________    H      H O H      H H H                                                                                ##STR23##                                            H      H O H      H H H                                                                                ##STR24##                                            4-CF.sub.3                                                                           H O H      H H H                                                                                ##STR25##                                            4-CF.sub.3                                                                           H O H      H H H                                                                                ##STR26##                                            4-CF.sub.3                                                                           H O H      H H H                                                                                ##STR27##                                            4-Br   H O H      H H H                                                                                ##STR28##                                            3-CF.sub.3                                                                           H O H      H H H                                                                                ##STR29##                                            3-CF.sub.3                                                                           H O H      H H H                                                                                ##STR30##                                            4-F    H O H      H H H                                                                                ##STR31##                                            4-F    H O H      H H H                                                                                ##STR32##                                            4-F    H O H      H H H                                                                                ##STR33##                                            4-F    H O H      H H H                                                                                ##STR34##                                            4-F    H O H      H H H                                                                                ##STR35##                                            4-F    H O H      H H H                                                                                ##STR36##                                            4-F    H O H      H H H                                                                                ##STR37##                                            4-F    H O H      H H H                                                                                ##STR38##                                            4-Cl   H O H      H H H                                                                                ##STR39##                                            4-OCHF.sub.2                                                                         H O H      H H H                                                                                ##STR40##                                            4-F    H O H      H H H                                                                                ##STR41##                                            4-F    H O H      H H H                                                                                ##STR42##                                            4-F    H O CH.sub.3                                                                             H H H                                                                                ##STR43##                                            4-F    H O COOCH.sub.3                                                                          H H H                                                                                ##STR44##                                            4-F    H S H      H H H                                                                                ##STR45##                                            4-Cl   H O H      H H H                                                                                ##STR46##                                            4-Cl   H O H      H H H                                                                                ##STR47##                                            4-Cl   H O H      H H H                                                                                ##STR48##                                            4-Cl   H O H      H H H                                                                                ##STR49##                                            4-OCHF.sub.2                                                                         H O H      H H H                                                                                ##STR50##                                            4-OCHF.sub.2                                                                         H O H      H H H                                                                                ##STR51##                                            4-OCHF.sub.2                                                                         H O H      H H H                                                                                ##STR52##                                            4-OCHF.sub.2                                                                         H O H      H H H                                                                                ##STR53##                                            4-OCH.sub.2 CF.sub.3                                                                 H O H      H H H                                                                                ##STR54##                                            4-OCH.sub.2 CF.sub.3                                                                 H O H      H H H                                                                                ##STR55##                                            4-CF.sub.3                                                                           H O H      H H H                                                                                ##STR56##                                            __________________________________________________________________________

                  TABLE 1B                                                        ______________________________________                                         ##STR57##                                                                    Y      Z     X     R2  R.sup.3                                                                            R.sup.4                                                                            R.sup.5                                                                           R.sup.6                                  ______________________________________                                        4-CF.sub.3                                                                           H     O     H   H    H    H                                                                                  ##STR58##                               H      H     O     H   H    H    H                                                                                  ##STR59##                               4-t.-butyl                                                                           H     O     H   H    H    H                                                                                  ##STR60##                               3-CF.sub.3                                                                           H     O     H   H    H    H                                                                                  ##STR61##                               4-CH.sub.3                                                                           H     O     H   H    H    H                                                                                  ##STR62##                               4-CH.sub.3                                                                           H     O     H   H    H    H                                                                                  ##STR63##                               4-Cl   H     O     H   H    H    H                                                                                  ##STR64##                               4-Cl   H     O     H   H    H    H                                                                                  ##STR65##                               4-F    H     O     H   H    H    H                                                                                  ##STR66##                               4-Cl   H     O     H   CH.sub.3                                                                           H    H                                                                                  ##STR67##                               4-OCHF.sub.2                                                                         H     O     H   CH.sub.3                                                                           H    H                                                                                  ##STR68##                               4-F    H     O     H   CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                  ##STR69##                               4-CF.sub.3                                                                           H     O     H   H    H    H                                                                                  ##STR70##                               4-Cl   H     O     H   H    H    H                                                                                  ##STR71##                               4-Br   H     O     H   H    H    H                                                                                  ##STR72##                               4-Cl   H     O     H   H    H    H                                                                                  ##STR73##                               ______________________________________                                    

                                      TABLE 1C                                    __________________________________________________________________________     ##STR74##                                                                    Y    Z X R.sup.2                                                                              R.sup.3                                                                          R.sup.4                                                                         R.sup.5                                                                         R.sup.6                                                __________________________________________________________________________    H    H O H      H  H H                                                                                ##STR75##                                             H    H O H      H  H H                                                                                ##STR76##                                             4-CF.sub.3                                                                         H O H      H  H H                                                                                ##STR77##                                             4-CF.sub.3                                                                         H O H      H  H H                                                                                ##STR78##                                             4-CF.sub.3                                                                         H O H      H  H H                                                                                ##STR79##                                             4-Br H O H      H  H H                                                                                ##STR80##                                             3-CF.sub.3                                                                         H O H      H  H H                                                                                ##STR81##                                             3-CF.sub.3                                                                         H O H      H  H H                                                                                ##STR82##                                             4-Br H O H      H  H H                                                                                ##STR83##                                             4-F  H O H      H  H H                                                                                ##STR84##                                             4-F  H O H      H  H H                                                                                ##STR85##                                             4-F  H O H      H  H H                                                                                ##STR86##                                             4-F  H O H      H  H H                                                                                ##STR87##                                             4-F  H O H      H  H H                                                                                ##STR88##                                             4-F  H O H      H  H H                                                                                ##STR89##                                             4-F  H O H      H  H H                                                                                ##STR90##                                             4-Cl H O H      H  H H                                                                                ##STR91##                                             4-OCHF.sub.2                                                                       H O H      H  H H                                                                                ##STR92##                                             4-F  H O H      H  H H                                                                                ##STR93##                                             4-F  H O H      H  H H                                                                                ##STR94##                                             4-F  H O CH.sub.3                                                                             H  H H                                                                                ##STR95##                                             4-F  H O COOCH.sub.3                                                                          H  H                                                                                ##STR96##                                               4-F  H S H      H  H H                                                                                ##STR97##                                             4-F  H O H      CH.sub.3                                                                         H H                                                                                ##STR98##                                             4-Cl H O H      H  H H                                                                                ##STR99##                                             4-Cl H O H      H  H H                                                                                ##STR100##                                            4-Cl H O H      H  H H                                                                                ##STR101##                                            4-Cl H O H      H  H H                                                                                ##STR102##                                            4-OCHF.sub.2                                                                       H O H      H  H H                                                                                ##STR103##                                            4-OCHF.sub.2                                                                       H O H      H  H H                                                                                ##STR104##                                            __________________________________________________________________________

                                      TABLE 1D                                    __________________________________________________________________________     ##STR105##                                                                   Y      Z X  R.sup.2                                                                         R.sup.3                                                                          R.sup.4                                                                          R.sup.5                                                                         R.sup.6                                                 __________________________________________________________________________    4-OCHF.sub.2                                                                         H O  H H  H  H                                                                                ##STR106##                                             4-OCHF.sub.2                                                                         H O  H H  H  H                                                                                ##STR107##                                             4-OCH.sub.2 CF.sub.3                                                                 H O  H H  H  H                                                                                ##STR108##                                             4-OCH.sub.2 CF.sub.3                                                                 H O  H H  H  H                                                                                ##STR109##                                             4-CF.sub.3                                                                           H O  H H  H  H                                                                                ##STR110##                                             4-CF.sub.3                                                                           H O  H H  H  H                                                                                ##STR111##                                             H      H O  H H  H  H                                                                                ##STR112##                                             4-t.-butyl                                                                           H O  H H  H  H                                                                                ##STR113##                                             3-CF.sub.3                                                                           H O  H H  H  H                                                                                ##STR114##                                             4-CH.sub.3                                                                           H O  H H  H  H                                                                                ##STR115##                                             4-CH.sub.3                                                                           H O  H H  H  H                                                                                ##STR116##                                             4-Cl   H O  H H  H  H                                                                                ##STR117##                                             4-Cl   H O  H H  H  H                                                                                ##STR118##                                             4-F    H O  H H  H  H                                                                                ##STR119##                                             4-Cl   H O  H CH.sub.3                                                                         H  H                                                                                ##STR120##                                             4-OCHF.sub.2                                                                         H O  H CH.sub.3                                                                         H  H                                                                                ##STR121##                                             4-F    H O  H CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                ##STR122##                                             4-CF.sub.3                                                                           H O  H H  H  H                                                                                ##STR123##                                             4-Cl   H O  H H  H  H                                                                                ##STR124##                                             4-Br   H O  H H  H  H                                                                                ##STR125##                                             4-Cl   H O  H H  H  H                                                                                ##STR126##                                             __________________________________________________________________________

                                      TABLE 1E                                    __________________________________________________________________________     ##STR127##                                                                   Y    Z  X R.sup.2                                                                             R.sup.3                                                                          R.sup.4                                                                         R.sup.5                                                                         R.sup.6                                                __________________________________________________________________________    H    H  O H     H  H H                                                                                ##STR128##                                            H    H  O H     H  H H                                                                                ##STR129##                                            4-CF.sub.3                                                                         H  O H     H  H H                                                                                ##STR130##                                            4-CF.sub.3                                                                         H  O H     H  H H                                                                                ##STR131##                                            4-CF.sub.3                                                                         H  O H     H  H H                                                                                ##STR132##                                            4-Br H  O H     H  H H                                                                                ##STR133##                                            3-CF.sub.3                                                                         H  O H     H  H H                                                                                ##STR134##                                            3-CF.sub.3                                                                         H  O H     H  H H                                                                                ##STR135##                                            4-F  H  O H     H  H H                                                                                ##STR136##                                            4-F  H  O H     H  H H                                                                                ##STR137##                                            4-F  H  O H     H  H H                                                                                ##STR138##                                            4-F  H  O H     H  H H                                                                                ##STR139##                                            4-F  H  O H     H  H H                                                                                ##STR140##                                            4-F  H  O H     H  H H                                                                                ##STR141##                                            4-F  H  O H     H  H H                                                                                ##STR142##                                            4-F  H  O H     H  H H                                                                                ##STR143##                                            4-Cl H  O H     H  H H                                                                                ##STR144##                                            4-OCHF.sub.2                                                                       H  O H     H  H H                                                                                ##STR145##                                            4-F  H  S H     H  H H                                                                                ##STR146##                                            4-F  H  O CH.sub.3                                                                            H  H H                                                                                ##STR147##                                            4-F  H  O COOCH.sub.3                                                                         H  H H                                                                                ##STR148##                                            4-F  H  O H     CH.sub.3                                                                         H H                                                                                ##STR149##                                            4-F  H  S H     H  H H                                                                                ##STR150##                                            4-Cl 3-Cl                                                                             O H     H  H H                                                                                ##STR151##                                            4-Cl H  O H     H  H H                                                                                ##STR152##                                            4-Cl H  O H     H  H H                                                                                ##STR153##                                            4-Cl H  O H     H  H H                                                                                ##STR154##                                            4-OCHF.sub.2                                                                       H  O H     H  H H                                                                                ##STR155##                                            4-OCHF.sub.2                                                                       H  O H     H  H H                                                                                ##STR156##                                            __________________________________________________________________________

                                      TABLE 1F                                    __________________________________________________________________________     ##STR157##                                                                   Y      Z X  R.sup.2                                                                         R.sup.3                                                                          R.sup.4                                                                          R.sup.5                                                                         R.sup.6                                                 __________________________________________________________________________    4-OCHF.sub.2                                                                         H O  H H  H  H                                                                                ##STR158##                                             4-OCHF.sub.2                                                                         H O  H H  H  H                                                                                ##STR159##                                             4-OCH.sub.2 CF.sub.3                                                                 H O  H H  H  H                                                                                ##STR160##                                             4-OCH.sub.2 CF.sub.3                                                                 H O  H H  H  H                                                                                ##STR161##                                             4-CF.sub.3                                                                           H O  H H  H  H                                                                                ##STR162##                                             4-CF.sub.3                                                                           H O  H H  H  H                                                                                ##STR163##                                             H      H O  H H  H  H                                                                                ##STR164##                                             4-t.-butyl                                                                           H O  H H  H  H                                                                                ##STR165##                                             3-CF.sub.3                                                                           H O  H H  H  H                                                                                ##STR166##                                             4-CH.sub.3                                                                           H O  H H  H  H                                                                                ##STR167##                                             4-CH.sub.3                                                                           H O  H H  H  H                                                                                ##STR168##                                             4-Cl   H O  H H  H  H                                                                                ##STR169##                                             4-Cl   H O  H H  H  H                                                                                ##STR170##                                             4-F    H O  H H  H  H                                                                                ##STR171##                                             4-Cl   H O  H CH.sub.3                                                                         H  H                                                                                ##STR172##                                             4-OCHF.sub.2                                                                         H O  H CH.sub.3                                                                         H  H                                                                                ##STR173##                                             4-F    H O  H CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                ##STR174##                                             4-CF.sub.3                                                                           H O  H H  H  H                                                                                ##STR175##                                             4-Cl   H O  H H  H  H                                                                                ##STR176##                                             4-Br   H O  H H  H  H                                                                                ##STR177##                                             4-Cl   H O  H H  H  H                                                                                ##STR178##                                             __________________________________________________________________________

                  TABLE 1G                                                        ______________________________________                                         ##STR179##                                                                   Y      Z     X     R.sup.2                                                                           R.sup.3                                                                           R.sup.4                                                                           R.sup.5                                                                           R.sup.6                                    ______________________________________                                        H      H     O     H   H   H   H                                                                                  ##STR180##                                H      H     O     H   H   H   H                                                                                  ##STR181##                                4-CF.sub.3                                                                           H     O     H   H   H   H                                                                                  ##STR182##                                4-CF.sub.3                                                                           H     O     H   H   H   H                                                                                  ##STR183##                                4-CF.sub.3                                                                           H     O     H   H   H   H                                                                                  ##STR184##                                4-Br   H     O     H   H   H   H                                                                                  ##STR185##                                3-CF.sub.3                                                                           H     O     H   H   H   H                                                                                  ##STR186##                                3-CF.sub.3                                                                           H     O     H   H   H   H                                                                                  ##STR187##                                4-F    H     O     H   H   H   H                                                                                  ##STR188##                                4-F    H     O     H   H   H   H                                                                                  ##STR189##                                4-F    H     O     H   H   H   H                                                                                  ##STR190##                                4-F    H     O     H   H   H   H                                                                                  ##STR191##                                4-F    n     O     H   H   H   H                                                                                  ##STR192##                                4-F    H     O     H   H   H   H                                                                                  ##STR193##                                4-F    H     O     H   H   H   H                                                                                  ##STR194##                                4-F    H     O     H   H   H   H                                                                                  ##STR195##                                4-Cl   H     O     H   H   H   H                                                                                  ##STR196##                                4-OCHF.sub.2                                                                         H     O     H   H   H   H                                                                                  ##STR197##                                4-F    H     S     H   H   H   H                                                                                  ##STR198##                                ______________________________________                                    

                                      TABLE 1H                                    __________________________________________________________________________     ##STR199##                                                                   Y      Z  X R.sup.2                                                                             R.sup.3                                                                          R.sup.4                                                                          R.sup.5                                                                         R.sup.6                                             __________________________________________________________________________    4-F    H  O CH.sub.3                                                                            H  H  H                                                                                ##STR200##                                         4-F    H  O COOCH.sub.3                                                                         H  H  H                                                                                ##STR201##                                         4-F    H  O H     H  H  H                                                                                ##STR202##                                         4-F    H  O H     CH.sub.3                                                                         H  H                                                                                ##STR203##                                         4-Cl   3-Cl                                                                             O H     H  H  H                                                                                ##STR204##                                         4-Cl   H  O H     H  H  H                                                                                ##STR205##                                         4-Cl   H  O H     H  H  H                                                                                ##STR206##                                         4-Cl   H  O H     H  H  H                                                                                ##STR207##                                         4-OCHF.sub.2                                                                         H  O H     H  H  H                                                                                ##STR208##                                         4-OCHF.sub.2                                                                         H  O H     H  H  H                                                                                ##STR209##                                         4-OCHF.sub.2                                                                         H  O H     H  H  H                                                                                ##STR210##                                         4-OCHF.sub.2                                                                         H  O H     H  H  H                                                                                ##STR211##                                         4-OCH.sub.2 CF.sub.3                                                                 H  O H     H  H  H                                                                                ##STR212##                                         4-OCH.sub.2 CF.sub.3                                                                 H  O H     H  H  H                                                                                ##STR213##                                         4-CF.sub.3                                                                           H  O H     H  H  H                                                                                ##STR214##                                         4-CF.sub.3                                                                           H  O H     H  H  H                                                                                ##STR215##                                         H      H  O H     H  H  H                                                                                ##STR216##                                         4-t.-butyl                                                                           H  O H     H  H  H                                                                                ##STR217##                                         3-CF.sub.3                                                                           H  O H     H  H  H                                                                                ##STR218##                                         4-CH.sub.3                                                                           H  O H     H  H  H                                                                                ##STR219##                                         4-SCH.sub.3                                                                          H  O H     H  H  H                                                                                ##STR220##                                         4-Br   H  O H     H  H  H                                                                                ##STR221##                                         4-Cl   H  O H     H  H  H                                                                                ##STR222##                                         4-F    H  O H     H  H  H                                                                                ##STR223##                                         4-Cl   H  O H     CH.sub.3                                                                         H  H                                                                                ##STR224##                                         4-OCHF.sub.2                                                                         H  O H     CH.sub.3                                                                         H  H                                                                                ##STR225##                                         4-F    H  O H     CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                ##STR226##                                         4-CF.sub.3                                                                           H  O H     H  H  H                                                                                ##STR227##                                         4-Cl   H  O H     H  H  H                                                                                ##STR228##                                         4-Br   H  O H     H  H  H                                                                                ##STR229##                                         4-F    H  O H     H  H  H                                                                                ##STR230##                                         __________________________________________________________________________

                                      TABLE 1I                                    __________________________________________________________________________     ##STR231##                                                                   Y      Z  X R.sup.2                                                                              R.sup.3                                                                         R.sup.4                                                                         R.sup.5                                                                         R.sup.6                                              __________________________________________________________________________    H      H  O H      H H H                                                                                ##STR232##                                          H      H  O H      H H H                                                                                ##STR233##                                          4-CF.sub.3                                                                           H  O H      H H H                                                                                ##STR234##                                          4-CF.sub.3                                                                           H  O H      H H H                                                                                ##STR235##                                          4-CF.sub.3                                                                           H  O H      H H H                                                                                ##STR236##                                          4-Br   H  O H      H H H                                                                                ##STR237##                                          3-CF.sub.3                                                                           H  O H      H H H                                                                                ##STR238##                                          3-CF.sub.3                                                                           H  O H      H H H                                                                                ##STR239##                                          4-F    H  O H      H H H                                                                                ##STR240##                                          4-F    H  O H      H H H                                                                                ##STR241##                                          4-F    H  O H      H H H                                                                                ##STR242##                                          4-F    H  O H      H H H                                                                                ##STR243##                                          4-F    H  O H      H H H                                                                                ##STR244##                                          4-F    H  O H      H H H                                                                                ##STR245##                                          4-F    H  O H      H H H                                                                                ##STR246##                                          4-F    H  O H      H H H                                                                                ##STR247##                                          4-Cl   H  O H      H H H                                                                                ##STR248##                                          4-OCHF.sub.2                                                                         H  O H      H H H                                                                                ##STR249##                                          4-F    H  O H      H H H                                                                                ##STR250##                                          3,4-OCF.sub.2 O                                                                         O H      H H H                                                                                ##STR251##                                          4-Cl   H  O H      H H H                                                                                ##STR252##                                          4-F    H  O H      H H H                                                                                ##STR253##                                          4-F    H  O H      H H H                                                                                ##STR254##                                          4-Cl   H  O COOCH.sub.3                                                                          H H H                                                                                ##STR255##                                          4-Cl   H  O H      H H H                                                                                ##STR256##                                          4-Cl   H  O H      H H H                                                                                ##STR257##                                          4-Cl   H  O H      H H H                                                                                ##STR258##                                          4-OCHF.sub.2                                                                         H  O H      H H H                                                                                ##STR259##                                          4-OCHF.sub.2                                                                         H  O H      H H H                                                                                ##STR260##                                          __________________________________________________________________________

                                      TABLE 1K                                    __________________________________________________________________________     ##STR261##                                                                   Y       Z  X  R.sup.2                                                                          R.sup.3                                                                          R.sup.4                                                                          R.sup.5                                                                          R.sup.6                                             __________________________________________________________________________    4-OCHF.sub.2                                                                          H  O  H  H  H  H                                                                                 ##STR262##                                         4-OCHF.sub.2                                                                          H  O  H  H  H  H                                                                                 ##STR263##                                         4-OCH.sub.2 CF.sub.3                                                                  H  O  H  H  H  H                                                                                 ##STR264##                                         4-OCH.sub.2 CF.sub.3                                                                  H  O  H  H  H  H                                                                                 ##STR265##                                         4-CF.sub.3                                                                            H  O  H  H  H  H                                                                                 ##STR266##                                         4-CF.sub.3                                                                            H  O  H  H  H  H                                                                                 ##STR267##                                         H       H  O  H  H  H  H                                                                                 ##STR268##                                         4-t.-butyl                                                                            H  O  H  H  H  H                                                                                 ##STR269##                                         3-CF.sub.3                                                                            H  O  H  H  H  H                                                                                 ##STR270##                                         4-CH.sub.3                                                                            H  O  H  H  H  H                                                                                 ##STR271##                                         4-CH.sub.3                                                                            H  O  H  H  H  H                                                                                 ##STR272##                                         4-Cl    H  O  H  H  H  H                                                                                 ##STR273##                                         4-Cl    H  O  H  H  H  H                                                                                 ##STR274##                                         4-F     H  O  H  H  H  H                                                                                 ##STR275##                                         4-Cl    H  O  H  CH.sub.3                                                                         H  H                                                                                 ##STR276##                                         4-OCHF.sub.2                                                                          H  O  H  CH.sub.3                                                                         H  H                                                                                 ##STR277##                                         4-F     H  O  H  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                 ##STR278##                                         4-CF.sub.3                                                                            H  O  H  H  H  H                                                                                 ##STR279##                                         4-Cl    H  O  H  H  H  H                                                                                 ##STR280##                                         4-Br    H  O  H  H  H  H                                                                                 ##STR281##                                         4-Cl    H  O  H  H  H  H                                                                                 ##STR282##                                         __________________________________________________________________________

                                      TABLE 1L                                    __________________________________________________________________________     ##STR283##                                                                   Y         Z X R.sup.2                                                                             R.sup.3                                                                          R.sup.4                                                                          R.sup.5                                                                         R.sup.6                                           __________________________________________________________________________    H         H O H     H  H  H                                                                                ##STR284##                                       H         H O H     H  H  H                                                                                ##STR285##                                       4-CF.sub.3                                                                              H O H     H  H  H                                                                                ##STR286##                                       4-CF.sub.3                                                                              H O H     H  H  H                                                                                ##STR287##                                       4-CF.sub.3                                                                              H O H     H  H  H                                                                                ##STR288##                                       4-Br      H O H     H  H  H                                                                                ##STR289##                                       3-CF.sub.3                                                                              H O H     H  H  H                                                                                ##STR290##                                       3-CF.sub.3                                                                              H O H     H  H  H                                                                                ##STR291##                                       4-F       H O H     H  H  H                                                                                ##STR292##                                       4-F       H O H     H  H  H                                                                                ##STR293##                                       4-F       H O H     H  H  H                                                                                ##STR294##                                       4-F       H O H     H  H  H                                                                                ##STR295##                                       4-F       H O H     H  H  H                                                                                ##STR296##                                       4-F       H O H     H  H  H                                                                                ##STR297##                                       4-F       H O H     H  H  H                                                                                ##STR298##                                       4-F       H O H     H  H  H                                                                                ##STR299##                                       4-Cl      H O H     H  H  H                                                                                ##STR300##                                       4-OCHF.sub.2                                                                            H O H     H  H  H                                                                                ##STR301##                                       4-F       H O CH.sub.3                                                                            H  H  H                                                                                ##STR302##                                       4-O(CH.sub.2).sub.2 CH.sub.3                                                            H O H     H  H  H                                                                                ##STR303##                                       4-F       H O CH.sub.3                                                                            H  H  H                                                                                ##STR304##                                       4-F       H O COOCH.sub.3                                                                         H  H  H                                                                                ##STR305##                                       4-F       H O H     H  H  H                                                                                ##STR306##                                       4-Cl      H O H     H  H  H                                                                                ##STR307##                                       4-Cl      H O H     H  H  H                                                                                ##STR308##                                       4-Cl      H O H     H  H  H                                                                                ##STR309##                                       4-Cl      H O H     H  H  H                                                                                ##STR310##                                       4-OCHF.sub.2                                                                            H S H     H  H  H                                                                                ##STR311##                                       4-OCHF.sub.2                                                                            H O H     H  H  H                                                                                ##STR312##                                       4-OCHF.sub.2                                                                            H O H     H  H  H                                                                                ##STR313##                                       4-OCHF.sub.2                                                                            H O H     H  H  H                                                                                ##STR314##                                       4-OCH.sub.2 CF.sub.3                                                                    H O H     H  H  H                                                                                ##STR315##                                       4-OCH.sub.2 CF.sub.3                                                                    H O H     H  H  H                                                                                ##STR316##                                       4-Br      H O H     H  H  H                                                                                ##STR317##                                       4-Cl      H O H     H  H  H                                                                                ##STR318##                                       H         H O H     H  H  H                                                                                ##STR319##                                       4-t.-butyl                                                                              H O H     H  H  H                                                                                ##STR320##                                       3-CF.sub.3                                                                              H O H     H  H  H                                                                                ##STR321##                                       4-CH.sub.3                                                                              H O H     H  H  H                                                                                ##STR322##                                       4-CH.sub.3                                                                              H O H     H  H  H                                                                                ##STR323##                                       4-Cl      H O H     CH.sub.3                                                                         H  H                                                                                ##STR324##                                       4-Cl      H O H     H  H  H                                                                                ##STR325##                                       4-Br      H O H     H  H  H                                                                                ##STR326##                                       4-O(CH.sub.2).sub.2 CH.sub.3                                                            H O H     CH.sub.3                                                                         H  H                                                                                ##STR327##                                       4-OCHF.sub.2                                                                            H O H     CH.sub.3                                                                         H  H                                                                                ##STR328##                                       4-F       H O H     CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                ##STR329##                                       4-CF.sub.3                                                                              H O H     H  H  H                                                                                ##STR330##                                       4-Cl      H O H     H  H  H                                                                                ##STR331##                                       4-Cl      H O H     H  H  H                                                                                ##STR332##                                       __________________________________________________________________________

                                      TABLE M                                     __________________________________________________________________________     ##STR333##                                                                   Y          Z  X  R.sup.2                                                                             R.sup.3                                                                          R.sup.4                                                                          R.sup.5                                                                           R.sup.6                                      __________________________________________________________________________    H          H  O  H     H  H  H                                                                                  ##STR334##                                  H          H  O  H     H  H  H                                                                                  ##STR335##                                  4-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR336##                                  H          H  O  H     H  H  H                                                                                  ##STR337##                                  4-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR338##                                  4-Br       H  O  H     H  H  H                                                                                  ##STR339##                                  3-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR340##                                  3-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR341##                                  4-F        H  O  H     H  H  H                                                                                  ##STR342##                                  4-F        H  O  H     H  H  H                                                                                  ##STR343##                                  4-F        H  O  H     H  H  H                                                                                  ##STR344##                                  4-F        H  O  H     H  H  H                                                                                  ##STR345##                                  4-F        H  O  H     H  H  H                                                                                  ##STR346##                                  4-F        H  O  H     H  H  H                                                                                  ##STR347##                                  4-F        H  O  H     H  H  H                                                                                  ##STR348##                                  4-F        H  O  H     H  H  H                                                                                  ##STR349##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR350##                                  4-OCHF.sub.2                                                                             H  O  H     H  H  H                                                                                  ##STR351##                                  4-F        H  O  H     H  H  H                                                                                  ##STR352##                                  4-Br       H  O  H     H  H  H                                                                                  ##STR353##                                  4-F        H  O  H     H  H  CH.sub.3                                                                           ##STR354##                                  4-Br       H  O  H     H  H  H                                                                                  ##STR355##                                  4-F        H  O  H     H  H  H                                                                                  ##STR356##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR357##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR358##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR359##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR360##                                  4-OCHF     2 H                                                                              O  H     H  H  H                                                                                  ##STR361##                                  4-OCHF.sub.2                                                                             H  O  H     H  H  H                                                                                  ##STR362##                                  4-OCHF.sub.2                                                                             H  O  H     H  H  H                                                                                  ##STR363##                                  4-OCHF.sub.2                                                                             H  O  H     H  H  H                                                                                  ##STR364##                                  4-OCH.sub.2 CF.sub.3                                                                     H  O  H     H  H  H                                                                                  ##STR365##                                  4-OCH.sub.2 CF.sub.3                                                                     H  O  H     H  H  H                                                                                  ##STR366##                                  4-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR367##                                  4-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR368##                                  4-O CH.sub.2CH.sub.3                                                                     H  O  H     H  H  H                                                                                  ##STR369##                                  4-t.-butyl H  O  H     H  H  H                                                                                  ##STR370##                                  3-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR371##                                  4-CH.sub.3 H  O  H     H  H  H                                                                                  ##STR372##                                  4-CH.sub.3 H  O  H     H  H  H                                                                                  ##STR373##                                  O(CH.sub.2).sub.2CH.sub.3                                                                H  O  H     H  H  H                                                                                  ##STR374##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR375##                                  4-F        H  O  H     H  H  H                                                                                  ##STR376##                                  4-Cl       H  O  H     CH.sub.3                                                                         H  H                                                                                  ##STR377##                                  4-OCHF     2 H                                                                              O  H     CH.sub.3                                                                         H  H                                                                                  ##STR378##                                  4-F        H  O  H     CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR379##                                  4-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR380##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR381##                                  4-Br       H  O  H     H  H  H                                                                                  ##STR382##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR383##                                  __________________________________________________________________________     ##STR384##                                                                   Y          Z  X  R.sup.2                                                                             R.sup.3                                                                          R.sup.4                                                                          R.sup.5                                                                           R.sup.6                                      __________________________________________________________________________    4-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR385##                                  4-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR386##                                  4-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR387##                                  4-Br       H  O  H     H  H  H                                                                                  ##STR388##                                  3-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR389##                                  3-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR390##                                  4-F        H  O  H     H  H  H                                                                                  ##STR391##                                  4-F        H  O  H     H  H  H                                                                                  ##STR392##                                  4-F        H  O  H     H  H  H                                                                                  ##STR393##                                  4-F        H  O  H     H  H  H                                                                                  ##STR394##                                  4-F        H  O  H     H  H  H                                                                                  ##STR395##                                  H          H  O  H     H  H  H                                                                                  ##STR396##                                  H          H  O  H     H  H  H                                                                                  ##STR397##                                  4-F        H  O  H     H  H  H                                                                                  ##STR398##                                  4-F        H  O  H     H  H  H                                                                                  ##STR399##                                  4-F        H  O  H     H  H  H                                                                                  ##STR400##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR401##                                  4-OCHF.sub.2                                                                             H  O  H     H  H  H                                                                                  ##STR402##                                  4-F        H  O  H     H  H  H                                                                                  ##STR403##                                  4-F        H  O  CH.sub.3                                                                            H  H  H                                                                                  ##STR404##                                  4-F        H  O  COOCH.sub.3                                                                         H  H  H                                                                                  ##STR405##                                  4-F        H  O  H     CH.sub.3                                                                         H  H                                                                                  ##STR406##                                  4-F        H  S  H     H  H  H                                                                                  ##STR407##                                  4-Cl       3-Cl                                                                             O  H     H  H  H                                                                                  ##STR408##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR409##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR410##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR411##                                  4-OCHF.sub.2                                                                             H  O  H     H  H  H                                                                                  ##STR412##                                  4-OCHF.sub.2                                                                             H  O  H     H  H  H                                                                                  ##STR413##                                  4-OCHF.sub.2                                                                             H  O  H     H  H  H                                                                                  ##STR414##                                  4-OCHF.sub.2                                                                             H  O  H     H  H  H                                                                                  ##STR415##                                  4-OCH.sub.2 CF.sub.3                                                                     H  O  H     H  H  H                                                                                  ##STR416##                                  4-OCH.sub.2 CF.sub.3                                                                     H  O  H     H  H  H                                                                                  ##STR417##                                  4-CF.sub.3 H  O  H     H  H  H                                                                                  ##STR418##                                  4-F        H  O  H     H  H  H                                                                                  ##STR419##                                  4-F        H  O  CH.sub.3                                                                            H  H  H                                                                                  ##STR420##                                  4-F        H  O  COOCH.sub.3                                                                         H  H  H                                                                                  ##STR421##                                  4-Cl       H  O  H     H  H  H                                                                                  ##STR422##                                  __________________________________________________________________________

If, for example, 3-(4'-chlorophenyl)-4-(4"-methyl-3"-trifluoromethyl-Δ²"-1",2","4-triazolin-5"-on-1"-yl)-4,5-dihydropyrazole and4-trifluoro-methoxy-phenyl isocyanate are used as starting materials,the course of the reaction of process (A) according to the invention canbe represented by the following equation: ##STR423## If, for example,N-(4-trifluoromethoxy)-3-(4'-chlorophenyl)-4-(4"-methyl-3"-trifluoromethyl-Δ²"-1",2",4"-triazolin-5"-on-1"-yl)-4,5-dihydro-1-pyrazole-carboxanilideand 2-iodopropane are used as starting materials, the course of thereaction of process (B) according to the invention can be represented asfollows: ##STR424##

Formula (II) provides a general definition of the pyrazoline derivativesrequired as starting materials for carrying out the process (A)according to the invention. In this formula (II), R¹, R², R³, R⁴, Y andZ preferably represent those radicals which have already been mentionedin connection with the description of the substances of the formula (I)according to the invention as being preferred for these substituents.The pyrazoline derivatives of the formula (II) are new and can beprepared by one of the following processes.

They are prepared by reacting compounds of the formula (VI) ##STR425##with hydrazine hydrate in a polar organic solvent, preferably analkanol, at temperatures from 20° to 80° C., in particular at 30° to 60°C.: ##STR426## Depending on the meaning of the substituents R³ and R⁴,this results in the following process variants of the starting compoundsof the formula (VI) ##STR427##

a) R³ and R⁴ in formula (VI) represent hydrogen ##STR428##

In this case, the reaction is carried out with a formalin solution in apolar organic solvent, preferably an alkanol and, in particular, inethanol or methanol, with addition of small amounts of an organic base,in particular piperidine, and addition of glacial acetic acid.

b) In the formula (VI), R³ represents alkyl or aryl and R⁴ representshydrogen: ##STR429##

The process conditions correspond to those in the reaction withformaldehyde.

c) In the formula (VI), R³ and R⁴ represent alkyl: ##STR430##

In this case, the compound (VI) is first converted into the salt using astrong base, and the product is subsequently reacted with a halide, inparticular an iodide of the formula ##STR431##

The compounds of the formula (VII) formed in this process is brominated,and the intermediate of the formula (IX) is subsequently prepared byadding a base and eliminating HBr.

Compounds of the formula (II) in which R³ and R⁴ represent hydrogen arefurthermore obtained by reacting compounds of the formula (VId)##STR432## in which

Y and Z have the abovementioned meaning and

R²⁻¹ represents hydrogen, alkyl or alkoxycarbonyl,

by first heating them, or, if appropriate, refluxing them, in a 1st stepin a polar organic solvent, preferably acetonitrile, at temperaturesfrom 10° to 100° C., in particular at 20° to 80° C., with one mole ofN,N-dimethylmethyleneimmonium chloride of the formula (XI), ##STR433##and the intermediate of the formula (XII) which is formed ##STR434## is,if appropriate, isolated and subsequently, in a second step, cyclisedwith hydrazine hydrate in a polar organic solvent, preferably analcohol, at temperatures from 20° to 80° C., in particular at 30° to 60°C., to give compounds of the formula (II).

Compounds of the formula (II) in which R³ represents the radical --CH₂--N(CH₃)₂ and R⁴ represents hydrogen are obtained by first heating, ifappropriate refluxing, in a 1st step, compounds of the formula (VId)##STR435## in which

Y and Z have the abovementioned meaning and

R²⁻¹ represents hydrogen, alkyl or alkoxycarbonyl,

with 2 mol of N,N-dimethylmethyleneimmonium chloride of the formula(XI), ##STR436## in a polar organic solvent, preferably acetonitrile, attemperatures from 10° to 100° C., in particular at 20° to 80° C., andthe intermediate of the formula (XIIa) which is formed ##STR437## is, ifappropriate, isolated and subsequently, in a second step, cyclised withhydrazine hydrate in a polar organic solvent, preferably an alcohol, attemperatures from 20° to 80° C., in particular at 30° to 60° C., to givecompounds of the formula (II) (cf. also the Preparation Example).##STR438##

Some of the compounds of the formula (VIa) and (VId) are new. They areprepared by reacting the compounds ##STR439## in which

R²⁻² represents hydrogen, alkyl or alkoxycarbonyl,

X and Y have the abovementioned meaning and

Hal represents halogen, in particular bromine, with the compound R¹ -Hwith the aid of an organic or inorganic base with the elimination ofhydrogen halide. The compounds of the formula (X) and R¹ -H are knownsubstances (cf., for example, Comprehensive Heterocyclic Chemistry, A.R. Katritzky, Vol. 5, Part 4A, Pergamon Press and U.S. Pat. No.3,780,052).

When carrying out the process according to the invention following theprocess variant ( B ), compounds of the formula (IV) ##STR440## in whichX, Y, Z, R¹, R², R⁴, R⁵ and R⁶ have the abovementioned meaning, arereacted with a strong base, preferably an organometal compound, inparticular with butyl-lithium, in the inert organic solvent attemperatures from -50° to 0° C., in particular from -30° C. to -15° C.,if appropriate in the presence of a protective-gas atmosphere, inparticular a rare-gas atmosphere such as, for example, argon, and theproduct is subsequently reacted with a halide Hal-R²

in which

R²⁻² represents alkyl, optionally substituted cycloalkyl, halogenoalkyl,alkoxycarbonyl or halogenoalkylthio,

at 0° to 60° C., in particular at -10° to -40° C., and the mixture isworked up in the customary manner by adding water and extracting themixture with ether.

This gives compounds of the formula (XIII) ##STR441## in which X, Y, Z,R¹, R², R³, R⁴, R⁵, R⁶ and R⁹ have the abovementioned meanings.

The active compounds are suitable for combating-animal pests, preferablyarthropods and nematodes, in particular insects and arachnids, whichoccur in agriculture, in animal keeping, in forests, in the protectionof stored products and of materials, and in the hygiene sector. They areactive against normally sensitive and resistant species and against allor individual development stages.

The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp. From the order of the Homoptera, for example,Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphisgossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralispomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae,Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelisbilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae,Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii,Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelidesobtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsadecemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodeschrysocephala, Epilachna varive stis, Atomaria spp., Oryzaephilussurinamensis, Antho nomus spp., Sitophilus spp., Otiorrhynchus sulcatus,Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica,Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctusspp., Meligethes aeneus, Ptinus spp., Niptus hololeucus,Gibbiumpsylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solsti tialis andCostelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomoriumpharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Hydrotaea spp.,Haematobia spp., Glossina spp., Melophagus spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis,Ceratophyllus spp. and Ctenocephalides spp.

From the order of the Arachnida for example Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Ornithonyssus spp., Eriophyesribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp.,Amblyomma spp., Hyalomma spp., Ixodes spp., Dermacentor spp.,Haemaphysalis spp., Otobius spp., Psoroptes spp., Chorioptes spp.,Sarcoptes spp., Psorergates spp., Demodex spp., Notoedres spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The active compounds according to the invention are not only activeagainst plant, hygiene and stored product pests, but also, in theveterinary medicine sector, against animal parasites (ectoparasites andendoparasites) such as scaly ticks, argasidae, scab mites, trombidae,flies (stinging and licking), parasitic fly larvae, lice, hair lice,bird lice, fleas and worms which live as endoparasites.

They are active against normally-sensitive and resistant species andstrains as well against all parasitic and non-parasitic developmentstages of the ecto- and endoparasites.

The active compounds according to the invention are distinguished by apowerful insecticidal and acaricidal activity.

They can be employed particularly successfully against insects which areharmful to plants such as, for example, against the larvae of themustard beetle (Phaedon cochleariae) or against the caterpillars of thecabbage moth (Plutella maculipennis) or against the tobacco budworm(Heliothis virescens).

Moreover, they can be employed particularly successfully for combatingpests of warm-blooded species which live as parasites such as, forexample, against blowfly larvae (Lucilia cuprina), against Muscadomestica and against Periplaneta americana.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, suspensions, powders, foams, pastes,granules, aerosols, natural and synthetic materials impregnated withactive compound, very fine capsules in polymeric substances and incoating compositions for seed, and furthermore into formulations usedwith burning equipment, such as fumigating cartridges, fumigating cans,fumigating coils and the like, as well as ULV cold mist and warm mistformulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is, emulsifying agents and/or dispersingagents, and/or foam-forming agents. In the case of the use of water asan extender, organic solvents can, for example, also be used asauxiliary solvents. As liquid solvents, there are suitable in the main:aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinatedaromatics or chlorinated ali phatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example mineral oilfractions, alcohols, such as butanol or glycol as well as their ethersand esters, ketones, such as acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents, such asdimethylformamide and dimethyl sulphoxide, as well as water; byliquefied gaseous extenders or carriers are meant liquids which aregaseous at ambient temperature and under atmospheric pressure, forexample aerosol propellants, such as halogenated hydrocarbons as well asbutane, propane, nitrogen and carbon dioxide; as solid carriers thereare suitable: for example ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as highly-disperse silica,alumina and silicates; as solid carriers for granules there aresuitable: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, as well as syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;as emulsifying and/or foam-forming agents there are suitable: forexample non-ionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates aswell as albumen hydrolysis products; as dispersing agents there aresuitable: for example ligninsulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc. The formulations in general containbetween 0.1 and 95 per cent by weight of active compound, preferablybetween 0.5 and 90%.

The active compounds according to the invention can be present in theircommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilising agents, acaricides, nematicides,fungicides, growth-regulating substances or herbicides. The insecticidesinclude, for example, phosphates, carbamates, carboxylates, chlorinatedhydrocarbons, phenylureas, substances produced by microorganisms and thelike.

The active compounds according to the invention can furthermore bepresent in their commercially available formulations and in the useforms, prepared from these formulations, as a mixture with synergisticagents. Synergistic agents are compounds which increase the action ofthe active compounds, without it being necessary for the synergisticagent added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompounds are distinguished by an excellent residual action on wood andclay as well as a good stability to alkali on limed substrates.

The active compounds according to the invention are also suitable forcombating insects, mites, ticks and the like in the field of animalkeeping and livestock breeding, so that, by combating the pests, betterresults, for example higher milk yield, higher weight, more beautifulanimal coat, longer life and the like, can be achieved.

In this field, the active compounds according to the invention areapplied in a known manner, such as by external administration in theform of, for example, dipping, spraying, pouring-on, spotting-on anddusting, as well by parenteral administration, for example in the formof an injection, and furthermore by the feed-through method. Besides,application as shaped articles (collar, ear mark), and application inthe form of the so-called environment treatment, are also possible.

The examples which follow describe the preparation and the use of activecompounds according to the invention without imposing any limitation.

PREPARATION EXAMPLES Example 1 ##STR442##

2.76 g (0,008 mol) of3-(4'-chlorophenyl)-4-(4"-methyl-3"-trifluoromethyl-Δ^(2")-1",2",4"-triazolin-5"-on-1"-yl)-4,5-dihydropyrazole are dissolved in 20ml of acetonitrile (anhydrous) at 60° C. until a clear solution hasformed, this solution is treated with 1.7 g of 4-trifluoromethoxy-phenylisocyanate, and 2drops of triethylamine are added. The mixture issubsequently allowed to stand for 2 hours at room temperature. Thesolvent is subsequently stripped off in vacuo, the residue is treatedwith 20 ml of diethyl ether and, after 2 hours, the precipitate whichhas formed is filtered off with suction. 2.0 g (45.6% of theory) ofN-(4-trifluormethoxy)-3-(4'-chlorophenyl)-4-(4"-methyl-3"-trifluoromethyl-Δ^(2")-1",2",4,"-triazolin-5"-on-1"-yl)-4,5-dihydro-1-pyrazole-carboxanilidehaving a melting point of 241° C. are obtained.

The end products of the formula (I) which are listed below in Table 2are obtained analogously to Example 1 and taking into consideration theinformation given in the description of the processes according to theinvention:

                                      TABLE 2                                     __________________________________________________________________________     ##STR443##                                                  (I)              Example                                                                       No.   R.sup.1          R.sup.2                                                                         R.sup.3                                                                             R.sup.4                                                                         R.sup.5                                                                         R.sup.6     Y  Z X Melting point                                                                 °C.              __________________________________________________________________________           ##STR444##      H H     H H                                                                                ##STR445## 4Cl                                                                              H O 211                     4                                                                                    ##STR446##      H H     H H                                                                                ##STR447## 4Cl                                                                              H O 241                     3                                                                                    ##STR448##      H H     H H                                                                                ##STR449## 4Cl                                                                              H O 218                     5                                                                                    ##STR450##      H H     H H                                                                                ##STR451## 4Cl                                                                              H O 230                     6                                                                                    ##STR452##      H H     H H                                                                                ##STR453## 4Cl                                                                              H O 256                     7                                                                                    ##STR454##      H H     H H                                                                                ##STR455## 4Cl                                                                              H O 257                     8                                                                                    ##STR456##      H H     H H                                                                                ##STR457## 4Cl                                                                              H O 192                     9                                                                                    ##STR458##      H H     H H                                                                                ##STR459## 4Cl                                                                              H O 226                     10                                                                                   ##STR460##      H H     H H                                                                                ##STR461## H  H O 224                     11                                                                                   ##STR462##      H H     H H                                                                                ##STR463## H  H O 238                     12                                                                                   ##STR464##      H H     H H                                                                                ##STR465## H  H O 236                     13                                                                                   ##STR466##      H H     H H                                                                                ##STR467## H  H O 204                     14                                                                                   ##STR468##      H H     H H                                                                                ##STR469## H  H O 221                     15                                                                                   ##STR470##      H H     H H                                                                                ##STR471## H  H O 203                     16                                                                                   ##STR472##      H H     H H                                                                                ##STR473## H  H O 241                     17                                                                                   ##STR474##      H                                                                                ##STR475##                                                                         H H                                                                                ##STR476## 4Cl                                                                              H O 229                     18                                                                                   ##STR477##      H H     H H                                                                                ##STR478## 4Cl                                                                              H O 234                     19                                                                                   ##STR479##      H                                                                                ##STR480##                                                                         H H                                                                                ##STR481## 4Cl                                                                              H O 242                     20                                                                                   ##STR482##      H H     H H                                                                                ##STR483## 4Cl                                                                              H O                         21                                                                                   ##STR484##      H H     H H                                                                                ##STR485## 4Cl                                                                              H O                         22                                                                                   ##STR486##      H H     H H                                                                                ##STR487## 4Cl                                                                              H O                         __________________________________________________________________________

PREPARATION OF THE STARTING COMPOUNDS Example (II-1) ##STR488##

11.2 g (0.035 mol) of α-(4-methyl-3-trifluoromethyl-Δ²-1,2,4-triazolin-5-on-1-yl)-4'-chloroaceto-phenone are dissolved in 100ml of absolute acetonitrile until a clear solution has formed, 10 g(0.107 mol) of N,N-dimethylmethyleneimmonium chloride are added, and themixture is refluxed for 4 hours until starting material is no longervisible following TLC checking. 20 ml of hydrazine hydrate are thenadded at 70° C., and stirring is continued for 10 minutes. The mixtureis subsequently concentrated in vacuo, the residue is treated with 200ml of water, and the mixture is extracted using ethyl acetate. Theorganic phase is separated, dried over MgSO₄ and concentrated. 12 g (99%of theory) of 3-(4"-chlorophenyl)-4-(4"-methyl-3"-trifluoromethyl-Δ^(2")-1",2",4"-triazolin-5"-on-1"-yl)-4,5-dihydropyrazole are obtained as apale yellow solid having a melting point of 198° C.

The starting compounds of the formula (II) which are listed below inTable 3 are obtained analogously to Example (II-1) and taking intoconsideration the information in the description of the processesaccording to the invention:

                                      TABLE 3                                     __________________________________________________________________________     ##STR489##                                                 (II)              Example No.                                                                          R.sup.1           R.sup.2                                                                         R.sup.3 R.sup.4                                                                         Y  Z Physical Constant                   __________________________________________________________________________    II-2                                                                                  ##STR490##       H H       H H  H .sup.1 H NMR*: (δ =                                                     7.3-7.75(5H, m); 6.05(1H, q);                                                 3.71-3.95(2H, m);  3.36(3H, s)      II-3                                                                                  ##STR491##       H H       H 4Cl                                                                              H oil                                 II-4                                                                                  ##STR492##       H CH.sub.2N(CH.sub.3).sub.2                                                             H 4Cl                                                                              H .sup.1 H NMR**: (δ =                                                    5.63(1H, d); 3.95(1H, m);                                                     2.20-2.45(2H, m); 2.2(6H,                                                     s)3.1(3H, s); 2.1(3H, s)            II-5                                                                                  ##STR493##       H H       H 4Cl                                                                              H oil                                 II-6                                                                                  ##STR494##       H H       H 4Cl                                                                              H oil                                 __________________________________________________________________________

PREPARATION OF THE PRECURSORS ##STR495##

1.8 g (0.075 mol) of sodium hydride are suspended in 100 ml of DMF(anhydrous) under a protective gas atmosphere, and 10 g (0.06 mol) of4-methyl-3-trifluoromethyl-Δ² -1,2,4-triazolin-5-one, dissolved in 100ml of DMF (anhydrous), are added dropwise to this suspension at 20° C.Stirring is subsequently continued for 3 hours at 60° C. until a clearsolution has formed. 14 g (0.06 mole) of 4-chlorophenacyl bromide,dissolved in 100 ml of DMF (anhydrous), are added dropwise to thissolution at 20° to 30° C., and stirring is then continued for 1 morehour at room temperature. The reaction mixture is treated with 2 l ofwater and the solid which precipitates is filtered off with suction andsubsequently resuspended in petroleum ether. After filtration withsuction, 11.5 g (52% of theory) of α-(4-methyl-3-trifluoromethyl-Δ²-1,2,4-triazolin-5-on- 1-yl)-4'-chloroacetophenone are obtained as apale yellow solid.

¹ H NMR* (δ=7.48-7.95 (4H,m) 5.37 (2H,s), 3.43 (3H,s).

The precursors of the formula (VIa) which are listed below in Table 4are obtained analogously to Example (VIa-1) and taking intoconsideration the information in the description of the processesaccording to the invention:

                  TABLE 4                                                         ______________________________________                                         ##STR496##                  (VIa)                                            Example                                Physical                               No.    R.sup.1             Y      Z   Constant                                ______________________________________                                        (VIa-2)                                                                               ##STR497##         H      H   oil                                     (VIa-3)                                                                               ##STR498##         4Cl    H   148° C.                          (VIa-4)                                                                               ##STR499##         4Cl    H   128° C.                          (VIa-5)                                                                               ##STR500##         4Cl    H   126° C.                          (VIa-6)                                                                               ##STR501##         4Br    H   141° C.                          (VIa-7)                                                                               ##STR502##         4Cl    H   112° C.                          (VIa-8)                                                                               ##STR503##         4Cl    H   oil                                     (VIa-11)                                                                              ##STR504##         4Cl    H                                           (VIa-9)                                                                               ##STR505##         4Cl    H                                           (VIa-10)                                                                              ##STR506##         4Cl    H                                           ______________________________________                                         *The .sup.1 H NMR spectra were recorded in deuterochloroform (CDCl.sub.3)     with tetramethylsilane (TMS) as the internal standard. The data given are     the chemical shift as δ value in ppm.                                   **The .sup.1 H NMR spectra were recorded in deuterated dimethyl sulphoxid     (CD.sub.3).sub.2 SO with tetramethylsilane (TMS) as the internal standard     The data given are the chemical shift as the δ value in ppm.       

Use Examples

In the Use Examples which follow, the compounds listed below wereemployed as comparison substances. ##STR507##

Triflumuron=2-chloro-N[[[4-(trifluoromethoxy)-phenyl]amino]-carbonyl]-benzamide(disclosed in: DE-A 2,601,780) ##STR508##

Sulprofos=O-ethyl O-(4-methylthio)-phenyl S-propyl dithiophosphate(disclosed in: DE-A 2,111,414)

Example A

Phaedon larvae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with mustard beetle larvae (Phaedon cochleariae) while theleaves are still moist.

After the specified time, the destruction in % is-determined. 100% meansthat all the beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, a superior activity compared with the prior art is shown,for example, by the following compounds of the Preparation Examples: 1,5, 6, 7, 8, 10, 11, 12, 13, 14 and 16.

Example B

Heliothis virescens test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soya bean shoots (Glycine max) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with the tobacco budworm (Heliothis virescens) while the leavesare still moist.

After the specified time, the destruction in % is-determined. 100% meansthat all the caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, a superior activity compared with the prior art is shown,for example, by the following compounds of the Preparation Examples: 1,5 and 9.

Example C

Plutella test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with mustard beetle larvae (Phaedon cochleariae) while theleaves are still moist.

After the specified time, the destruction in % is determined. 100% meansthat all the beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, a superior activity compared with the prior art is shown,for example, by the following compounds of the Preparation Examples: 1,10 and 11.

Example D

Blowfly larvae test

Test animals: Lucilia cuprina larvae

Emulsifier: 35 parts by weight of ethylene glycol monomethyl ether 35parts by weight of nonylphenol polyglycol ether

To produce a suitable preparation of active compound, three parts byweight of active compound are mixed with seven parts by weight of theabovementioned mixture and the resulting emulsion concentrate is dilutedwith water to the specific, desired concentration.

Approximately 20 resistant Lucilia cuprina larvae are introduced into atest tube which contains approximately 1 cm³ of horse meat and 0.5 ml ofthe preparation of active compound. After 24 hours, the activity of thepreparation of active compound is determined. 100% means that allblowfly larvae have been killed; 0% means that none of the blowflylarvae have been killed.

In this test, a superior activity compared with the prior art was shown,for example, by the following compounds of the Preparation Examples: 1,5, 8, 9, 10, 11, 12, 13, 14 and 16.

Example E

LT₁₀₀ test

Test animals: Musca domestica, strain WHO-N Solvent:

35 parts by weight of ethylene glycol monomethyl ether

35 parts by weight of nonylphenol polyglycol ether

To prepare a Suitable formulation, three parts by weight of activecompound are mixed with seven parts of the abovementionedsolvent/emulsifier mixture, and the resulting emulsion concentrate isdiluted with water to the specific, desired concentration.

2 ml of this preparation of active compound are pipetted onto filterpaper dishes (φ9.5 cm) which are located in Petrie dishes of a suitablesize. After the filter discs have dried, 25 test animals are introducedinto the Petrie dish and covered.

The condition of the test animals is monitored continuously for up to 6hours. The time required for a 100% knock-down effect is determined. Ifthe LT₁₀₀ has not been reached after 6 hours, the percentage ofknocked-down test animals is determined.

In this test, an LT₁₀₀ of 100 minutes was shown, for example, by thecompound of Preparation Example 8 at an exemplary concentration of 1000ppm of a.i.

We claim:
 1. A substituted carbamoylpyrazoline of the formula ##STR509##in which R¹ represents an azolinone, azolinethione or azolineiminoradical, optionally monosubstituted or di-substituted by identical ordifferent substituents and bonded via nitrogen, from the groupconsisting of ##STR510## in which one of the groups A or B representsnitrogen while the other (B or A) represents oxygen, sulphur, the group--N alkyl(C₁ -C₄) or a methylene group --CH₂ --,W represents oxygen,sulphur or the group --N alkyl (--CH₁ -C₄), and the substituents on theazolinone, azolinethione or azolineimino radicals are alkyl (C₁ -C₆),alkoxy (C₁ -C₆), alkyl (C₁ -C₆) thio, amino, alkyl (C₁ -C₆) amino,halogenoalkyl (C₁ -C₄), dialkyl (C₁ -C₆) amino, and phenyl which isoptionally substituted by halogen, alkyl (C₁ -C₄), alkoxy (C₁ -C₄),halogenoalkyl (C₁ -C₄), halogenoalkoxy(C₁ -C₄)- or halogenoalkyl (C₁-C₄)thio, R² represents hydrogen, alkyl (C₁ -C₆), or representscycloalkyl (C₃ -C₇) which is optionally substituted by halogen orhalogenoalkyl-(C₁ -C₄); or represents halogenoalkyl (C₁ -C₄),halogenoalkyl (C₁ -C₄) thio or alkoxy (C₁ -C₆)carbonyl, R³ representshydrogen, alkyl(C₁ -C₆) or a group ##STR511## in which R⁷ and R⁸ in eachcase independently of one another represent hydrogen, alkyl(C₁ -C₆), orphenyl which is optionally substituted by alkyl (C₁ -C₄), alkoxy(C₁-C₄), alkyl(C₁ -C₄)thio, halogen, halogenoalkyl(C₁ -C₄),halogenoalkoxy(C₁ -C₄) or halogenoalkyl (C₁ -C₄)thio and R⁹ representshydrogen, alkyl(C₁ -C₆) or optionally substituted phenyl, wherein thesubstituents are the same as those recited for R⁸, andn represents thenumbers 1 to 4, R⁴ represents hydrogen or alkyl (C₁ -C₆), R⁵ representshydrogen, alkyl (C₁ -C₆), phenyl or alkyl(C₁ -C₆)thio, R⁶ representsalkyl(C₁ -C₈) which is optionally substituted by halogen, halogenoalkyl(C₁ -C₄) or halogenoalkoxy (C₁ -C₄), or represents cycloalkyl (C₃ -C₇)which is optionally substituted by halogen, halogenoalkyl(C₁ -C₄) orhalogenoalkoxy(C₁ -C₄), or represents the radical ##STR512## in whichR¹⁰ and R¹¹ can be identical or different and represent halogen,alkyl(C₁ -C₆), nitro, cyano, halogenoalkyl(C₁ -C₄), alkoxy(C₁ -C₆),halogenoalkoxy(C₁ -C₄), alkyl(C₁ -C₄)thio, halogenoalkyl (C₁ -C₄)thio,or represent phenoxy or phenylthio, each of which is optionallysubstituted by halogen, halogenoalkyl (C₁ -C₄) or alkoxy(C₁ -C₄), orrepresents mono- or dialkylamino, each of which has 1 to 6 carbon atomsin the alkyl radical and each of which is optionally substituted byhalogen, alkoxy(C₁ -C₄) or halogenoalkyl(C₁ -C₄), or representcycloalkyl(C₃ -C₇) which is optionally substituted by alkyl (C₁ -C₄),alkoxy(C₁ -C₄), halogen or alkyl(C₁ -C₄)thio, or represent alkoxy(C₁ -C₄)carbonyl, alkenyl(C₂ -C₆)oxy, alkinyl(C₂ -C₈), alkyl(C₁ -C₄)thionyl,alkyl(C₁ -C₄ ) sulphonyl, halogenoalkyl (C₁ -C₄)thionyl, halogenoalkyl(C₁ -C₄) sulphonyl or halogenoalkoxy (C₁ -C₄ ) carbonyl, or in whichR¹⁰and R¹¹ together represent one of the following bivalent radicals##STR513## X represents oxygen or sulphur and Y and Z can be identicalor different and represent hydrogen, alkyl (C₁ -C₆), halogen,halogenoalkyl (C₁ -C₅), alkoxy(C₁ -C₆), alkyl(C₁ -C₅)thio,halogenoalkoxy(C₁ -C₄), halogenoalkyl (C₁ -C₄) thio, alkoxy (C₁ -C₄)carbonyl, halogenoalkoxy(C₁ -C₄)carbonyl, or represent phenoxy orphenylthio, each of which is optionally substituted by halogen, alkyl(C₁-C₄), alkoxy(C₁ -C₄) or halogenoalkyl(C₁ -C₄), or represent alkenyl(C₁-C₆)oxy, alkinyl (C₂ -C₆), alkyl (C₁ -C₄)thionyl, alkyl (C₁-C₄)sulphonyl, halogenoalkyl(C₁ -C₄)thionyl, halogenoalkyl (C₁ -C₄)sulphonyl, nitro or cyano, or in which Y and Z together represent3,4-methylenedioxy or 3,4-ethylenedioxy, each of which is optionallysubstituted by fluorine and/or chlorine.
 2. A substitutedcarbamoylpyrazoline according to claim 1, whereinR¹ represents anazolinone, azolinethione or azolineimino radical, optionallymonosubstituted or disubstituted by identical or different substituentsand bonded via nitrogen, from the group consisting of ##STR514## inwhich one of the groups A or B represents nitrogen and while the other(B or A) represents oxygen, sulphur or the group --N alkyl (C₁ -C₄ ) ora methylene group --CH₂ --, W represents oxygen, sulphur or the group--N alkyl(C₁ -C₄) and the substituents on the azolinone, azolinethioneor azolineino radicals are alkyl (C₁ -C₄), alkoxy (C₁ -C₄), alkyl (C₁-C₄)thio, amino, alkyl (C₁ -C₄)amino, halogenoalkyl(C₁ -C₄), dialkyl (C₁-C₂) amino and phenyl which is optionally substituted by fluorine,chlorine, bromine, methyl, ethyl, methoxy, ethoxy, halogenoalkyl(C₁-C₂), halogenoalkoxy(C₁ -C₂) or halogenoalkyl (C₁ -C₂)thio, R²represents hydrogen, alkyl (C₁ -C₄), or cycloalkyl (C₃ -C₆) which isoptionally substituted by fluorine, chlorine, bromine or halogenoalkyl(C₁ -C₃); or represents halogenoalkyl (C₁ -C₃), halogenoalkyl (C₁ -C₃)thio or alkoxy(C₁ -C₄) carbonyl, R³ represents hydrogen, alkyl (C₁ -C₄)or a group ##STR515## in which R⁷ and R⁸ in each case independently ofone another represent hydrogen, alkyl(C₁ -C₄), or phenyl which isoptionally substituted by methyl, ethyl, methoxy, ethoxy, methylthio,ethylthio, fluorine, chlorine, bromine, halogenoalkyl (C₁ -C₂),halogenoalkoxy(C₁ -C₂) or halogenoalkyl(C₁ -C₂) thio andR⁹ representshydrogen alkyl(C₁ -C₄), or phenyl, which is optionally monosubstitutedor polysubstituted by identical or different substituents, wherein thesubstituents are the same as those recited for R⁸ and n represents thenumbers 1, 2 or 3, R⁴ represents hydrogen or alkyl(C₁ -C₄), R⁵represents hydrogen, alkyl (C₁ -C₄), phenyl or alkyl(C₁ -C₃) thio, R⁶represents alkyl (C₁ -C₄) which is optionally substituted by fluorine,chlorine, bromine, halogenoalkyl (C₁ -C₃) or halogenoalkoxy (C₁ -C₃), orrepresents cycloalkyl(C₃ -C₆) which is optionally substituted byfluorine, chlorine, bromine, halogenoalkyl(C₁ -C₃) or halogenoalkoxy(C₁-C₃), or represents the radical ##STR516## which R¹⁰ and R¹¹ can beidentical or different and represent fluorine, chlorine, bromine,iodine, alkyl (C₁ -C₄), nitro, cyano, halogenoalkyl (C₁ -C₃), alkoxy(C₁-C₄), halogenoalkoxy (C₁ -C₃), alkyl(C₁ -C₃) thio or halogenoalkyl (C₁-C₃)thio, or represent phenoxy which is optionally substituted byfluorine, chlorine, bromine, halogenoalkyl (C₁ -C₃) or alkoxy(C₁ -C₄),or represent mono- or dialkylamino, each of which has 1 to 4 carbonatoms in the alkyl radical and each of which is optionally substitutedby fluorine, chlorine, bromine, alkoxy(C₁ -C₃) or halogenoalkyl(C₁ -C₃),or represent cycloalkyl(C₃ -C₆) which is optionally substituted byalkyl(C₁ -C₃), alkoxy(C₁ -C₃), fluorine, chlorine, bromine or alkyl (C₁-C₃ ) thio, or in which R¹⁰ and R¹¹ together represent one of thefollowing bivalent radicals ##STR517## X represents oxygen or sulphurand Y and Z can be identical or different and represent hydrogen,alkyl(C₁ -C₄), fluorine, chlorine, bromine, halogenoalkyl(C₁ -C₄),alkoxy(C₁ -C₄), alkyl (C₁ -C₄) thio, halogenoalkoxy (C₁ -C₃),halogenoalkyl (C₁ -C₃)thio, alkoxy(C₁ -C₃)carbonyl, or phenoxy orphenylthio, each of which is optionally substituted by fluorine,chlorine, bromine, alkyl (C₁ -C₃), alkoxy (C₁ -C₃) or halogenoalkyl(C₁-C₃), or represent alkenyl (C₂ -C₄)oxy, alkinyl(C₂ -C₄), alkyl(C₁-C₃)thionyl, alkyl(C₁ -C₄)sulphonyl, halogenoalkyl(C₁ -C₃)thionyl,halogenoalkyl (C₁ -C₃)sulphonyl, nitro or cyano, or in whichY and Ztogether represent 3,4-methylenedioxy or 3,4-ethylenedioxy, each ofwhich is optionally substituted by fluorine and/or chlorine.
 3. Asubstituted carbamoylpyrazoline according to claim 1, whereinR¹represents an azolinone, azolinethione or azolineimino radical, in eachcase optionally monosubstituted or disubstituted by identical ordifferentsubstituents and bonded via nitrogen, from the group consistingof ##STR518## in which one of the groups A or B represents nitrogenwhile other (B or A) represents oxygen, sulphur,

    --NCH.sub.3 or a methylene group --CH.sub.2 --,

W represents oxygen or sulphur, and the substituents on the azolinone,azolinethione or azolineimino radicals are methyl, ethyl, n-propyl,i-propyl, t-butyl, methoxy, methylthio, trifluoromethyl,chlorodifluoromethyl, fluorodichloromethyl, and phenyl which isoptionally substituted by fluorine, chlorine, bromine, methyl, methoxy,trifluoromethyl or trifluoromethoxy R² represents hydrogen, methyl,ethyl, n-propyl, i-propyl or alkoxy(C₁ -C₂)carbonyl, R³ representshydrogen, methyl, ethyl, n-propyl, i-propyl or the group ##STR519## inwhich R⁷ and R⁸ in each case independently of one another representhydrogen, methyl, ethyl, n-propyl or i-propyl, R⁴ represents hydrogen,methyl, ethyl or n-propyl, R⁵ represents hydrogen, methyl, ethyl,n-propyl, i-propyl, phenyl or alkyl(C₁ -C₂)thio, R⁶ represents methyl,ethyl, n-propyl or i-propyl, each of which is optionally substituted byfluorine, chlorine, halogenoalkyl(C₁ -C₃) or halogenoalkoxy(C₁ -C₃), orrepresents cycloalkyl(C₃ -C₆) which is optionally substituted byfluorine, halogenoalkyl (C₁ -C₃) or halogenochlorine, alkoxy (C₁ -C₃),or represents the radical ##STR520## in which R¹⁰ and R¹¹ can beidentical or different and represent fluorine, chlorine, bromine,iodine, methyl, ethyl, n-propyl, i-propyl, tert. -butyl, nitro, cyano,halogenoalkyl(C₁ -C₃), alkoxy(C₁ -C₃), halogenoalkoxy (C₁ -C₃), alkyl(C₁-C₃)thio, halogenoalkyl (C₁ -C₃) thio, or represent phenoxy which isoptionally substituted by fluorine, chlorine, halogenoalkyl(C₁ -C₃),methoxy, ethoxy, methyl or ethyl, or represent mono- or dialkylamino,each of which has 1 to 3 carbon atoms in the alkyl radical and each ofwhich is optionally substituted by fluorine, chlorine, methoxy, ethoxyor halogenoalkyl (C₁ -C₃), or represent cycloalkyl (C₃ -C₆) which isoptionally substituted by methyl, ethyl, methoxy, ethoxy, fluorine,chlorine or alkyl (C₁ -C₃) thio, or in which R¹⁰ and R¹¹ togetherrepresent one of the following bivalent radicals ##STR521## X representsoxygen or sulphur and Y and Z can be identical or different andrepresent hydrogen, methyl, ethyl, n-propyl, i-propyl, fluorine,chlorine, halogenoalkyl (C₁ -C₃), methoxy, ethoxy, n-propyloxy,i-propyloxy, alkyl(C₁ -C₃)thio, halogenoalkoxy(C₁ -C₃), halogenoalkyl(C₁-C₃)thio, alkoxy(C₁ -C₃)carbonyl, or represent phenoxy or phenylthio,each of which is optionally substituted by fluorine, chlorine, methyl,ethyl, methoxy, ethoxy or halogenoalkyl (C₁ -C₃), or representalkenyl(C₃ -C₄)oxy , alkinyl(C₂ -C₄), alkyl(C₁ -C₃)thionyl, alkyl(C₁-C₃)sulphonyl, halogenoalkyl (C₁ -C₃)thionyl, halogenoalkyl (C₁-C₃)sulphonyl, nitro or cyano, or in which Y and Z together represent3,4-methylenedioxy or 3,4-ethylenedioxy, each of which is optionallysubstituted by fluorine and/or chlorine.
 4. A pesticidal compositioncomprising a pesticidally effective amount of a substitutedcarbamoylpyrazoline according to claim 1, and an inert diluent orcarrier.
 5. A method of combating pests which comprises contacting thepests and/or their environment with a pesticidally effective amount of asubstituted carbamoylpyrazoline according to claim 1.